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The Lost Art of Date Planning

By Cara Strickland

November 27, 2018

When I was younger, I remember spending a lot of time thinking about dating—what would it be like? I started stashing away ideas for cute dates I read about or watched in movies. I would be ready. But when I actually got into the dating pool, it seemed like date planning was a thing of the past.

Sure, almost every first date was coffee, but couldn’t we come up with something fun to do after that? Too often it felt like dates were a sort of default. We’d watch a movie or go to dinner because we couldn’t think of anything better to do.

No matter what stage you are in your relationship (or even if it isn’t officially one yet) date planning is a way to show that you’re paying attention, that you’re creative, and that you care. Plus, with the right activity, you can use your dates for what they were originally intended to do—give both of you the opportunity to see each other in a variety of contexts and get to know each other better.

Here are a few ideas to get you started.

Back To Childhood

Sometimes there is nothing better than returning to something you used to love as a kid. Whether that’s ice skating, swinging at the park, or playing air hockey at the local arcade (or arcade bar).

Have a conversation with your date about the sorts of things they enjoyed as children and find ways to integrate those happy memories into your time together. You might end up playing Monopoly, or Play Doh, or coloring. Either way, you’ll be making new memories while accessing old ones (and many of these activities give you plenty of time to talk).

Your Interest’s Interests

There’s nothing sexier than a date who pays attention to your preferences. Hopefully you have that date, but you can be that date as well. Is your guy into beer? Consider a local tasting or brewery tour (even a homebrewing class). Does your lady love old movies? See if any local theaters play them on the big screen. Once you’re aware of the types of activities someone enjoys, you’ll start to notice them everywhere.

These outings can be spendy, if you’re ready to take that step (think theater or concert tickets, or a coursed dinner) but they don’t have to be (why not try a local trivia night themed to their favorite fandom, wander through a shop they’ll love, or do something creative together—painting, ceramics, or whatever else floats their boat).

No matter what your date is into, choosing activities that compliment their interests will show that you care about them. Hopefully, they’ll soon be really into you.

Surprise, Surprise

When you’ve known someone for a little while, long enough to establish trust (and let them know your allergies) there can be something completely exciting about planning a surprise date. Maybe you pack a picnic and take it to the park at the end of the workweek, close enough to hear the live music. It might be a surprise trip to a nearby town and a walk along the lake. Whatever you do, make sure that your date is okay with surprises and that nothing about it will make them feel uncomfortable or unprepared (don’t plan to go swimming without giving your date a chance to pack a swimsuit). Surprise dates are an opportunity to show that you know this person well enough to delight them without their input—be sure that’s what you’re doing.

Back to Basics

There’s a reason why I paid attention to the dates in movies and books. Most of those characters aren’t spending an hour talking about what to watch on Netflix over pizza. While those night can be lovely, there’s something romantic about taking the time to actively choose an activity in advance. Subscribe to your local community calendar and get out of your comfort zone. Once you start, I’ll bet you’ll discover all kinds of events going on in your locale that you’d never have known about.

Take this opportunity to try new things together, you never know when you’ll discover something you really enjoy doing, or a new place you love (and it’s especially fun to discover those things with someone you’re getting to like very much).

Whatever you do, try to be mindful about your dates. Are you defaulting much of the time? Or are you engaged with the process? There’s no time like the present to shake up your routine. Who knows, it might be more fun than you’d thought dating could be.

Cara Strickland writes about food and drink, mental health, faith and being single from her home in the Pacific Northwest. She enjoys hot tea, good wine, and deep conversations. She will always want to play with your dog. Connect with her on Twitter @anxiouscook.